


Lost Bet

by Damien, Harlow (Damien)



Series: /r/nosleep fanfics [6]
Category: Working at an Amusement Park - Girl_from_the_crypt
Genre: Choking, Clothed Sex, Demon Virgin With A Crush, F/M, Gratuitous Smut, Snowballing
Language: English
Status: Completed
Published: 2020-05-12
Updated: 2020-05-12
Packaged: 2021-03-02 22:07:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,976
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24144100
Author URL: https://archiveofourown.org/users/Damien/pseuds/Damien, https://archiveofourown.org/users/Damien/pseuds/Harlow
Summary: Leah thought she'd win at blackjack and humiliate Mitchell by making him wear a skirt to the park during their off season, but dumb luck let him win. She's only got one skirt in her closet, and the Cowboy, along with most of the rest of the staff, find it pretty hot.
Relationships: Cowboy | Warin/Leah (Working at an Amusement Park)
Series: /r/nosleep fanfics [6]
Series URL: https://archiveofourown.org/series/1699717
Comments: 4
Kudos: 18





	Lost Bet

Mitchell flipped the card, showing the Queen. “And that’s 20, baby, that’s 3 wins!” He pumped his fists in the air, nearly knocking into the table.

Leah picked up his cup and drained it, letting out a belch when she finished. “Fuck off, best 5 of 7?” At his laugh, she flipped him off. “Seriously hate you, Sheriff Fuckface.”

He just laughed harder, coming around the table to put her in a tight hug that crushed her face into his chest. “Love you, little Leah.” He mumbled, kissing the top of her head. “You’re gonna kill Oliver for sure. Probably Darius too, and he’s like, the least sexual human being ever. Fuck, you might kill Maxine too. Definitely would look better than me!” He released her, wanderingly slightly drunkenly in search of another cup of beer.

——

Leah smoothed her skirt down, tugging at the hem to try and make it cover more. Tights and leggings were against the bet when she was sure Mitchell would lose, but his sheer dumb luck had her beat. She had convinced him to let her wear thigh highs, hers a more or less skin tone color just to keep her normally covered legs warm. The only skirt she could find in her closet was a little pleated plaid thing, and she debated, for half a second, going full school girl with a white button up and pigtails, but she liked her coworkers and didn’t want to risk anyone getting weird with her over clothes. Instead, she wore her normal boots and a black band shirt with a hoodie over it. It reminded her of high school, so she put her hair up into a pony tail and did a little dark makeup. She skipped straight past letting Mr Scratch out to head into Twin Vale Point.

Walking past Darius, she heard him whisper “Holy shit!” To himself, but he didn’t stop her, and she didn’t stop to talk to him. She had one focus, and that was on showing Mitchell she followed through.

Nathan stopped the stage coach next to the entrance when he saw her coming, struggling not to laugh. “Nice outfit.” He called to her, pointedly looking her up and down. “You look like a straight boy in the 90’s wet dream.”

Leah rolled her eyes, coming around to hop up next to him. “What a disgustingly vivid way to explain it. I’m looking for Mitch, I lost a bet. I’ve got to show him I followed through, and keep it on throughout the staff meeting, then I can change.” She felt the slight lurch as the coach started rolling, and she leaned back into the seat.

Nathan looked at her out of the corner of his eye, thinking. “If he doesn’t pop a boner looking at you, he’s gayer than me. Especially if he sees that garter.” Nathan nodded his head toward her, and Leah struggled to pull her skirt down more. Nathan just chuckled a little to himself, shaking his head.

Leah was focused on looking for Mitchell that she barely noticed the Cowboy looking up at the stage coach with wide eyes. He was watching them roll past, and he seemed to be a little more pink than normal. She didn’t take much of a note of it, instead giving him a tiny smile as they passed him and going back to looking for Mitchell.

Her coworker had stopped walking and was leaning against a wall, watching them come around. He didn’t notice until he stepped up close to Leah just how short her skirt was. He held out his hand, helping her hop down, and he had a little blush on his face. “Thanks, Nathan,” he said, giving Nathan a smile. In return, he got a slight huff of laughter, and Nathan took off again.

Leah tugged the skirt again, only managing to cover the top of her thigh highs. “I only had one skirt, so here I am, wearing a skirt.” She let him stare for a few seconds before she spoke. “Earth to Mitchell, come in Mitchell,” as she walked up closer. “I didn’t have any like, hippy girl floor length skirts, unfortunately. I almost had to buy one, but this skirt was buried under a couple other things I wore in high school.”

Mitchell’s jaw slammed shut as he realized how much he was staring, and he instead took out his phone. Before Leah could slap it out of his hand, he managed to get a few pictures of her. She looked cute, and even the pissed off expression added to it, somehow. As he looked through the pictures, he noticed the Cowboy in the background of two of them. He looked up, and the Cowboy was sitting on a fence rail. “I know, she’s hot as fuck, isn’t she?” Mitchell asked him, earning more of a blush and then a scowl.

Leah turned around, giving the Cowboy a little smile. “Hey,” she called, giving him a big smile. “You have Mitchell to thank for this outfit, he’s an asshole and I lost a bet.” The Cowboy’s eyebrows raised at that, and he tipped his hat to Mitchell. Leah shook her head, giggling a little. “You guys are just the same sometimes, huh?”

Mitchell shrugged, giving her a tiny smile. “I really expected you to be in like, a pencil skirt or something way less hot, to be real with you. You’re still like a little sister, but a hot little stepsister or something.”

Leah snorted, breaking into giggles. In her best imitation of the stereotype, she raised her hands to her cheeks and yelled “What are you doing, step bro?!” She broke into giggles, and the Cowboy just looked confused when Mitchell started to laugh a second later. “God, I think I broke Darius on my way over here, and I don’t even want to know what Oliver is gonna say.”

Mitchell took her arm, looping his into hers. “Well, we could get settled in for the meeting before everyone else arrives, and maybe we’ll find out if Dale’s into chicks.” He tugged her past the Cowboy, whose eyes followed them with interest.

——

“And please don’t do anything stupid, even if it’s funny, and especially not for snapchat or instagram or something.” Dale finished, his eyes lingering on Oliver, then Mitchell. “Any questions?” He asked, already moving half a step toward the door.

Everyone more or less just shook their heads, Anne and Caroline the only ones really focused. Leah kept tugging on her skirt, like she could make more fabric appear somehow, and it was very distracting. At the non-answer, Dale started toward the door. “Alright, don’t be stupid and don’t get us sued. I’d say have a good day today, but you lot would probably do something that would become my problem, so just don’t do anything too stupid.”

When the door slammed behind Dale, Oliver turned toward Leah. “Holy shit I have no idea what he said at all, your fucking legs!” He yelled, standing up. “Those fucking thighs should be illegal, and I’m gonna go dunk my head in an ice bucket or something because holy shit!”

Caroline and Maxine started to fold the chairs to put them aside, and Anne pulled Leah aside. “You look too cute,” she said, hugging Leah tight. “Even Dale kept looking at you then looking away, and Oliver’s right, kind of. You do look hot as hell, girl!” She laughed, and Leah laughed along with her. “i’ll go drag Max back to our section before she says something she’ll regret, but if you need any of our help with Mr Scratch given your outfit, let us know, okay?” She gave Leah’s arm a squeeze, then swerved past Darius and Mitchell, who were in conversation.

Leah thought about seeing what they were saying, but decided it wasn’t probably something she wanted to hear if she wanted things not to be weird with her and her section-mate. Instead, she headed outside, catching the Cowboy staring at her immediately. “Hey,” she said, walking past him toward her section. “What’s up, Cowboy?” She asked, only to have him follow slowly behind her. She stopped, turning around, and held out her hand. “You can walk with me, but I’d rather you walk next to me.”

He nodded, folding her hand into the crook of his arm as Mitchell had. He kept looking over at her, his face heating up more and more, especially when she caught him. He looked off, pretending he hadn’t been checking her out, and she stopped, watching his face. “What’s up, Cowboy? You keep looking at me, and I know I look different but I’m the same person I’ve always been.”

He shook his head, pulling away and looking at the skirt. She sighed, rolling her eyes. “I know, I know, it’s weird to see me in a skirt.” He shook his head quickly, and Leah tilted hers. “Not weird?” He shook his head again, his blush becoming stronger. “Oh, are you another person here who’s way too into it?”

He cleared his throat, not looking at her, and he took her hand again. She let him, her hands sliding up his arms. They felt strong, and what she’d seen of him the first time he unbuttoned his shirt for her did too, if you ignored the bullet holes. She liked being admired, but it felt weird. She let the Cowboy walk her to the sign for her section, but she surprised both of them by pulling him along. The Nurse was sitting by the roller coaster, and that meant the hospital was empty.

She pulled his arm toward the building, surprised with how quick he complied. She only stopped pulling him when he stumbled toward the front desk she sat on, only to have her yank down on his shirt to kiss him. She wrapped her legs around him as she pressed little pecks to his lips, not surprised when he leaned in and grabbed her hips with his big hands. He pulled her closer, his teeth tugging lightly on her lower lip and earning him a hitch in her breathing.

Leah smiled at him, unzipping her hoodie and letting it fall away. Her shirt was tight, and she could practically watch the second the Cowboy started staring at her nipples. Her bra was thin, and he was practically drooling on her while looking.

He pushed her shoulders back, and she leaned back on her hands. Her skirt was just long enough that even with her legs spread wide, he couldn’t see anything. He pushed her shirt up to the underside of her bra, then dug his fingers into her thighs. He slid his hands up the thin nylon material, stopping where he felt bare skin. His hands were buried under her skirt, and he leaned forward, nipping tiny little bites on her neck and getting her to squirm under him.

He yanked her mostly off the desk, laying her back. He flipped the skirt up, seeing the tiny black panties, and he groaned. He walked his fingers up her legs, looking up at her, and suddenly looked embarrassed. She pushed him down gently, watching him fall to his knees. He looked up at her, willing to follow orders, and Leah let out a shaky breath at the eager look on his face. He was made to serve, and he looked like that was all he wanted to do.

Leah smirked down at him, then lazily traced a line from the side of her knee up the inside of her thigh, to the bare flesh there. “Kiss,” she told him, and he did. He traced a line of little kisses up, then did the same to her other leg without prompting. With his lips still against the inside of her thigh, he looked up to her face, then gently bit her. Her eyebrows twitched and she let out a little noise, but not much of a reaction. He moved to the other thigh, giving her a slightly harder bite, and she moaned just loud enough to be audible. He sucked a mark into her skin, then smiled up at her again, before moving to bite then mark her other thigh. She practically slapped his hat off as she reached to grab his head, her nails scratching his scalp as she pulled his hair. He let her tilt his head back, his breathing a little hard, and he stared up at her, waiting for more instructions.

She looked down at his mouth, debating how good it’d feel to teach him exactly what she liked, but as it was, she had no idea when Darius would come back. The park was closed, but the last thing she needed would be Darius catching her with the Cowboy’s face buried under her skirt. She tugged his shirt, her voice quiet in the silent room. “You’re gonna fuck me,” she said, her own cheeks turning almost as red as his.

He let her cup the bulge in his pants, and she had his zipper down before he stopped her, undoing the button and sliding them down with his underwear. His cock was the same light tan as the rest of his skin, and Leah stared, her bottom lip between her teeth. He leaned over her, kissing her, and she kissed back, feeling him rub his fingers over her panties. He wasn’t sure what exactly to do, but he was enthusiastic and she appreciated it. She wrapped her arms around his neck, kissing him gently, and his fingers got a little more clumsy.

He managed to hook the side of her panties, yanking them aside, and he stroked over her bare pussy. He slid a finger into her, feeling her wetness, then he immediately pulled it out. He took two tries to line himself up properly, but then he slid inside. His eyes went Wide, and Leah wrapped her legs tight around him. He started slow and shallow, adjusting to the feeling.

Leah tilted her head, letting the Cowboy’s lips go to her neck and the bare line of shoulder where the neck of her shirt had been slid away. He bit into her shoulder, not hard enough to leave a mark but hard enough to muffle his moaning. He thrust deeper, barely aware of anything but how amazing it felt to be buried in her. Her hand slid down between them, rubbing her clit. “I’m gonna need you to go faster, I don’t want to risk getting caught,” she whispered, her hand going back to his hair and pulling it. He adjusted his angle a little, thrusting much harder and faster. She tipped her head back, her voice getting louder as she got closer and closer.

He struggled to not immediately fill her with his cum, trying his best to give her the rough fucking she wanted. When he brought a hand up and gently held her throat, he could feel her clench a little. He squeezed, slamming into her, and she slid her hand to his chest from between her legs, undoing two buttons with her shaky hand. She shoved her hand under his shirt, her nails raking marks down his back as he kept going. She shifted under him, getting him to hit the right spots, and her moaning and clenching was getting him close, especially with the little pain of her nails digging into his skin and pulling his hair.

He wanted to hold out until she came, but he didn’t quite make it, his clumsy hand coming down to try and rub at her clit to make it feel better for her. He was too close, though, and when he finally got the right angle for her clit, she clenched tight. He came hard, his only focuses on rubbing her clit and squeezing her throat. He was rewarded with her orgasm when she heard how hard he was panting, and she knew it was from her body. He was looking down at her with pure lust, and that was enough for her. If he hadn’t had a hand on her throat she’d likely have screamed, and he kissed her sloppily.

He dropped to his knees again, his thumbs holding her open, and he buried his tongue into her. He slurped his cum out of her, then stood over her and pulled her head up by the ponytail. He took the opportunity to kiss her when her mouth opened to probably yell at him, spitting it into her mouth. Her eyes widened, and she pushed it back into his mouth, only to have him do the same again. She tried not to swallow any of it, but after a few times of passing it back and forth, he straightened up and broke the kiss. She swallowed, looking up at him with her chest heaving as she tried to catch her breath. “That was… unexpected,” she said, getting what looked like a sadistic grin for a split second before it warmed into an innocent smile. He kissed her gently, cupping her face, and then she straightened up. “Okay, before someone walks in, we’ve gotta get decent.”

She hopped off the desk, wiping the little bit of the Cowboy’s drool from her chin before straightening her panties and yanking down her shirt. He tucked himself back into his pants, and picked up his hat from the ground. He blew on it, his smirk not breaking, then he sat it back on his head. He gave her one more kiss, then tipped his hat. “See you later,” she whispered to him. “Be good.”

He just winked at her, heading out the front doors as Darius walked past them, thankfully not looking in as Leah tried to make it look like she hadn’t just gotten fucked.


End file.
